So I have a minor update: After working for about two weeks with an external monitor hooked up directly to my mac, and using a different docking station to connect my mouse and keyboard, I tried reconnecting the docking station that I had the issue described above with. For some inexplicable reason, everything now worked fine. For about three days. Now the issue is back.

Finally solved here: https://www.displaylink.org/forum/showthread.php?t=69473 Basically, it looks like you need to use DisplayLinks dedicated "cleaner" https://www.displaylink.org/forum/showthread.php?t=69473 Before installing version 1.11.0. No other forms of cleaning/reinstalling have been able to solve this for me. https://www.synaptics.com/products/displaylink-manager-graphics-connectivity-111?filetype=exe